


The Third Man

by frecklesarechocolate



Category: Supernatural
Genre: Blow Jobs, M/M, Matchmaking
Language: English
Status: Completed
Published: 2013-05-26
Updated: 2013-05-26
Packaged: 2017-12-13 01:34:11
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 4
Words: 5,584
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/818401
Author URL: https://archiveofourown.org/users/frecklesarechocolate/pseuds/frecklesarechocolate
Summary: <blockquote class="userstuff">
              <p>Jimmy helps Castiel.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

  * For [deans1911 (partialdifferential)](https://archiveofourown.org/gifts?recipient=deans1911+%28partialdifferential%29).



> Happy birthday, Chris!

 

There is a small part of his head that Jimmy's kept locked away from Castiel. He's always assumed that's where Jimmy keeps his memories of his wife and daughter, precious, deep memories that he doesn't want to share with anyone, let alone Castiel. They've come to a sort of detente in recent years, but it was hard won, and it's worked well enough for the two of them.

That's been fine for Cas, because there's enough going on outside his head that he really doesn't want to have to worry about what's going on inside. Cas knows that it's been horrible for Jimmy, feels bad about it even, but he's stuck inside the vessel, and there's nowhere else for him to go. The longer he's inside Jimmy (and that sentence will never not be weird for Jimmy), the harder it is for Cas to separate himself.

Cas likes to find quiet places to sit and contemplate sometimes, and then he lets Jimmy kind of take control of where their mind goes. Cas does his best to step aside and to give Jimmy some privacy for those times. One day, though, Jimmy doesn't let Cas slip into the background.

_Castiel_? and the voice is both extremely familiar and nothing at all like what comes out of Cas's mouth when he speaks. A tendril of some emotion, tentative, comes with the question.

"Yes?" 

_You know it would be all right with me, right? I mean, if you wanted to be with Dean?_ There's a tendril of some emotion, almost like a faint hand reaching out to grip Cas's shoulder. Cas is startled, not sure where this is coming from, not even sure what prompted Jimmy to bring this up.

Cas responds slowly, choosing his words with care. "I'm not sure what you mean?" It's said in such a way that makes it clear that Cas does, in fact, know exactly what Jimmy means, but the words are out, and there's nothing to be done about that now.

_Castiel_ , Jimmy says, and his voice is tired but fond. Cas wonders when Jimmy began to think of him fondly, because by all rights, Jimmy should be eternally angry with Cas. Jimmy should hate Cas with the power of a thousand burning suns. Jimmy should want to find a way to rid himself of this comet and go back to his normal life.

Except that's not possible. How do you go back to a normal life after being part of all the extraordinary things that Cas and the Winchesters are part of?

_Castiel_ , Jimmy says again, and Cas realizes that his mind has wandered, and he's effectively ignored Jimmy. He feels enough guilt as it is, no need to add this to the list.

"Apologies. I'm not sure what to say, Jimmy," Cas says. There's the sense of laughter bubbling up inside, the kind of laughter that is halfway between mirth and sadness. It ends in a long, audible sigh.

_Oh, Castiel._ If he had a body... no, if he had control of his own body, he'd be rubbing the bridge of his nose, a smile still playing about his lips. But he didn't, and all he could do was send out another wave of emotion: affection, frustration, irritation. _You love him._

Cas is silent for a long time, and Jimmy can sense that he's thinking about Dean, the feelings of love rolling off of him in deep waves. It was a little like that time that he took Claire and Amelia to California and they went to the beach. The waves were huge and powerful, and they knocked Claire over a lot, but every time she fell over she was up and giggling, dashing back into the spray. 

"I do," Cas says simply. He's known it for a long time, of course, but hasn't been sure what to do with the information. As an angel, this is not exactly the sort of thing he'd been built for. He's not a cupid; love doesn't come naturally to him. Then again, rebellion didn't come naturally to him either, not at first.

_Do you want..._ Jimmy begins hesitantly, but then he switches tactics. _I can help_.

Cas frowns, his brow crinkling inward. "How?"

The laughter comes again, and this time it's friendly, affectionate, even. _Castiel, I fell in love with and married my best friend. I can help you get together with yours._

"Why?" Cas asks after a moment.

There's a long pause as Jimmy thinks about it, and Cas thinks that Jimmy isn't going to answer when finally, he says, _Honestly? Because there's not much else to do in here. Also, I think that you do deserve happiness._

Cas startles, surprised. "Really? Even after all that..."

_Don't make me change my mind, Castiel. Do you want my help or not?_

Cas holds up his hands in surrender, even though he knows that Jimmy can't see him. Jimmy can sense what he's doing, anyway. "Yes. Yes, I do."

_Good. Ok, now, first..._


	2. Chapter 2

Jimmy's first piece of advice to Cas is to just sit back and observe. To watch how Dean interacts with him and to catalog the little things.

_Not to sound too creepy about it, Castiel, but I watched Amelia for months before I asked her out._

Cas smiles. "Dean complains that I stare too much."

Laughter. _You do stare. But it's like you're... I don't know, like you're drinking him in, like you can't get enough of him. It's not like you're seeing him, seeing how he's interacting with you. There's a difference._

So Cas watches Dean. He watches Dean come out of his room in the bunker, dressed in a new plaid shirt (he has a yellow one that Cas thinks looks particularly good on him, but it's not as nice as the red and blue one), heading toward the kitchen to get some coffee. Cas watches Dean cook pancakes and bacon or sausage (and sometimes both) for breakfast. Cas watches Dean move around the kitchen like it was a second home to him, and then he watches as Dean makes sure that Sam eats at least something "unhealthy, because that lettuce bullshit can only get you so far, Sammy."

Cas watches Dean catalog the items in the Men of Letters bunker, and he watches Dean laugh himself silly when Sam inadvertently knocks over an enormous box that is, for reasons unknown, filled to the brim with confetti. It gets everywhere, and Sam has to pick pieces of confetti out of his hair for the rest of the day.

Dean brushes by Cas in the hallway, even when he doesn’t have to. He stares at Cas when he thinks Cas isn’t looking (Cas is always looking), and he’ll clap Cas on the shoulder, leaving his hand to linger a little bit longer than is strictly necessary.

At the end of every day, Cas and Jimmy discuss what they've observed. Jimmy states categorically that it's clear that Dean feels very strongly toward Cas, if not the same way as Cas does.

"But what do I do about it?" Cas asks one night.

_Nothing yet. Something'll come up, I promise, Castiel._

They'd found a used furniture shop in town, down the street from a decent book store, and they bought an enormous couch that they could all flop down on if they wanted, and in the evenings, Dean insists that Cas sit down with him and watch television. They watch all manner of shows, but eventually Dean decides that he's going to "educate" Cas in the wonders of Star Trek.

"We're gonna watch 'em all, right from the beginning, Cas. It'll be awesome, I promise." Dean usually pauses here and says, "We might skip 'Spock's Brain' though. That one is awful."

Sam bows out at this point in the evenings, muttering to himself that he can't stand the sexual tension. "Dude, what have I told you about that? Kirk and Spock are just friends," Dean says.

Sam usually just waves his hand over his shoulder, but Cas hears him mutter, "I wasn't talking about Kirk and Spock."

So each evening finds Cas and Dean on the couch watching a couple of episodes of Star Trek. Dean usually sits at one end of the couch and Cas sits at the other, but one thing Cas has noticed is that Dean tends to sprawl. He sprawls out to the point where he's taking up just about half the couch.

One evening, Jimmy makes Cas wait until Dean has seated himself first. _Don't sit right at the far side of the couch, Castiel._ Cas frowns and sends a questioning thought back to Jimmy, who just chuckles. _Trust me, just sit a little closer to the middle._ Cas shrugs and does as Jimmy suggests.

As usual, by about halfway through the first episode, Dean is sprawled out again, and his hand is tapping his knee lightly. At first, Cas doesn't pay attention to this, riveted to the episode, one in which there are two Kirks, one weak and indecisive and the other strong and overbearing. But he sees the tapping of Dean's fingers out of the corner of his eye and he's drawn to it. He's not sure why, exactly, because he's used to Dean's constant state of movement.

_He's doing it on purpose, Castiel._

_Hm?_ Cas thinks.

 _He's doing it to get your attention._ There's a pause for a moment, and then Jimmy says, _Put your hand on the couch next to you. The one closest to Dean. Don't stop watching the television though._

Cas does as he's told, keeping his attention focused forward. He's holding himself so stiffly that he feels like he might break in half if there were the slightest push in the wrong spot.

 _Relax, Castiel. Breathe._ Jimmy sends a wave of calm toward Cas, who accepts it gratefully, exhaling slowly. His body loses some of its tension, and when he looks out of the corner of his eye at Dean, he realizes that Dean's hand has moved off his knee and is now on the couch next to Cas's hand.

 _What now?_ Cas asks, although he thinks he may already know.

 _Wait a little bit, and if Dean doesn't move his hand, you move yours,_ Jimmy says. _It's a pretty classic move, Castiel._

On screen, there's a confrontation between the two Kirks which ends in one of them screaming that he wants to live. As the next scene begins, Cas feels a warm palm slide onto his. As the two Kirks are transported out and one Kirk is transported back, Cas closes his fingers over Dean's hand and squeezes lightly. He risks a peek at Dean, who is studiously watching the television, but there's a small smile on his lips.

Jimmy sends a strong wave of approval toward Cas and then Cas can feel Jimmy slip into the background. Cas and Dean watch another episode, holding hands the entire time.

**Notes for the Chapter:**

> Dean and Cas are watching _The Enemy Within_.


	3. Chapter 3

Things between Dean and Cas escalate little by little after that night. Jimmy spends more and more time in the background, emerging every now and then to give Cas a small push. The steps that Cas and Dean take are small, incremental ones. They graduate from holding hands to sitting close together on the couch, fingers laced together in Dean’s lap. Sometimes Dean falls asleep in the middle of an episode, his head lolling on Cas’s shoulder. One night, Jimmy encourages Cas to sling his arm around Dean’s shoulder. 

“Dude, did you just pull the yawn and stretch on me?” Dean asks with a soft laugh. 

Cas looks at Dean blankly, but he can feel Jimmy’s laughter bubbling up inside.

 _Yawn and stretch?_ Cas thinks towards Jimmy a little bit later, after Dean falls into a doze.

Jimmy laughs again. _I’m sorry, Cas, I couldn’t resist._ Cas decides he doesn’t really mind, because Dean’s snaked his arm around Cas’s waist and has snuggled in closer.

A few days later, Cas can sense that Jimmy has something to say. There’s a humming vibration of energy that’s becoming increasingly difficult for Cas to ignore, and so he excuses himself to his room in the bunker. He doesn’t much like the room, it’s too spartan, too spare, but he has so few belongings, and it’s not like he really needs much in the way of stuff anyway. So he generally spends as little time there as possible. His sudden desire to go back to his room garners a strange look from Dean, but no comment.

“What is it, Jimmy?” Cas asks once he’s safely ensconced behind closed doors. He’s not exactly sure why he’s been keeping his conversations with Jimmy to himself, but he has. Jimmy hasn’t said anything about it, leaving Cas to assume that Jimmy is fine with the status of things.

 _You should ask him out on a date_ , Jimmy says, and of all the things that Cas had been expecting Jimmy to say, this was not one of them.

“What?” Cas sits down heavily on the bed. It’s not that comfortable, the mattress is old and a little lumpy, but he hadn’t complained - he doesn’t really need to sleep.

 _Well, you guys have been doing the cuddling and watching tv thing for a few weeks now, it might be time to graduate._ Jimmy’s voice has a tone of fondness to it. _It’s time, Cas._

“I don’t know... What kind of date?” Despite himself, Cas is curious about the idea. He remembers Emanuel going on a few dates with Daphne, where they would eat a small meal together and then walk through the town holding hands. The memories are fuzzy though, as if they’re hidden behind a veil of sheer cloth - he can see himself going through those motions, but there’s no emotion attached to them. The thought of doing something like that with Dean at once excites and terrifies Cas. 

 _For my first date with Amelia..._ Jimmy pauses, as if he’s trying to make a decision. Finally, there’s the sensation of a long exhale. _For our first date, I took Amelia to the State Fair. We ate so much food. Hot dogs, funnel cake, cotton candy. Amelia looked so beautiful._

It felt to Cas as if a Rubicon had been crossed, as if Jimmy had decided to let Cas in on a part of his memories that up until now had been jealously guarded. Cas waited silently for Jimmy to go on. 

 _I won her a stuffed tiger in the ring toss. I’d never won anything at a fair before... It was a cheap thing, but Amelia kept it for years._ Jimmy trails off, lost in his memories. Cas does his best to step aside, to stay out of the memories that Jimmy has dredged up, but he can’t help but feel the strong emotions that Jimmy’s associated with his first date with Amelia. Excitement, jittery nervousness, affection and an overwhelming need to touch, to feel Amelia. Cas is familiar with these feelings, all of them associated with one Dean Winchester. 

There’s a heavy sigh, a sense of loss, and then Jimmy says, _You should take him to dinner. There’s got to be a nice restaurant in town._

“Okay,” Cas says. He thinks about talking to Jimmy about Amelia for a moment, but Jimmy’s closed himself off again, and Cas is reminded that there are parts of Jimmy’s memories that are clearly marked “Not for Castiel.” These must be some of those.

Cas isn’t sure how exactly to go about asking Dean on a date, but he figures that going with the direct approach is probably the best. He waits until that evening when they’re watching Star Trek (they’ve moved into the second season now, an episode where most of the characters age rapidly). 

Cas is surprised to find that his palms are sweaty, and he rubs them on his - well, Dean’s - jeans. This time Dean’s arm is around Cas’s shoulders. Cas snuggles back into Dean’s arms, and gathers his courage. 

_You can do this, Cas._

“Dean.” 

“Hm? Yeah, Cas?”

“I’d like to go out on a date with you.”

Dean freezes for a second, and then grabs the remote control and pauses the tv. “What?” 

“A date. I’d like to go on a date with you. Dinner?”

Dean’s staring at him now, his mouth slightly agape and Cas is just about to take it back when he can practically feel Jimmy clamp down on his shoulder with an iron grip. _No, give him a minute._

Dean shakes his head slightly and then grins. “Yeah, Cas. I’d like that.”

Cas nods once. “Would Friday night be acceptable?”

“Sure,” Dean says. “That would be great.”

There’s a strong feeling of exultation coming from Jimmy. _Yes! You did it, Cas! Way to go!_  

They settle in and watch the rest of the episode. When Dean gets up to go to bed, he smiles shyly at Cas, like he’s a little bit surprised that they have a date on Friday, and Cas feels warm inside.

Friday night they go to dinner at the Italian restaurant in town. It’s a small, quiet spot with real tablecloths and candles in empty bottles of wine with wax drippings hanging over the sides. Cas is visibly nervous, and Dean just grins at him and grabs his hand, squeezing tightly. That helps Cas to relax, and they have a pleasant evening. The food is decent, and Cas enjoys watching Dean eat with his usual level of enthusiasm. 

After dinner, they walk back to the bunker slowly. Cas was surprised that Dean had agreed to walk in the first place, but he was secretly pleased. They are holding hands, and when they get back to the bunker, Cas begins to drop Dean’s hand, but Dean stops him. 

“Aren’t you going to walk me all the way to my door?” Dean asks. He’s got a twinkle in his eye, and Cas wonders if Dean is making fun of him. “Come on, it’s traditional to walk your date to their door.” Dean pulls Cas into the bunker and they walk down the hall to Dean’s room.

They pause outside Dean’s room, and Dean seems to be waiting for something. Cas scrubs the back of his neck, because he’s not really sure what to do next. _Kiss him, you idiot!_ Jimmy says, and it feels a bit like Jimmy gives him a giant shove. Cas licks his lips and leans up to press his mouth to Dean’s. 

Oh.

Dean’s lips move softly against Cas’s, and it’s just so nice. Cas shifts slightly, turning his head to the side so he can capture more of Dean’s mouth, and his hands come to rest on Dean’s hips. Dean cups Cas’s face with his own hands, and to Cas it feels a little like flying. After a few moments, Cas pulls away from Dean and he grins, feeling both centered and off balance all at once. Dean tugs on Cas’s hand and pulls him into the room.

Dean pushes Cas against the door and kisses him again, more insistent, his hands running through Cas’s hair. He’s muttering something, and at first Cas is so overwhelmed by the feel of Dean pressed against him that he doesn’t really register what Dean is saying, but Dean’s words become clear after a minute or so.

“Cas. Cas, want you,” Dean says. “Want this so bad. Need you.” Cas senses Jimmy pull back, way back, and he loses himself in the moment. Cas drags his fingers up Dean’s sides underneath the white dress shirt that he’s wearing, and Dean’s muttered litany is interrupted by a groan. Dean knocks his head back against the door, breaking the kiss. He stares down at Cas for a moment, and then grabs his hips and manoeuvres Cas backward toward the bed. Cas falls onto it and Dean crawls up over him, settling the weight of his chest on top of Cas’s. 

Dean smiles down at Cas. "Hi," he says, almost shy.

"Hello, Dean," Cas says, and he runs his fingers through Dean's hair. It's softer than he remembers it being, from all those years ago when he rebuilt this man. Dean leans into the touch, his eyes closed; some of the frenzy from their kissing has drained out of both of them. Dean shifts slightly so he's not leaning on his elbows and he rests his head on Cas's chest. Cas wraps an arm around Dean and kisses the top of his head.

"Cas," Dean says after a while of holding each other in silence.

"Mm?" Cas says sleepily. The rhythm of Dean's breathing against his torso has been lulling him to sleep. 

Dean props his chin on Cas's sternum and sees that Cas's eyes are drooping. He leans up and presses a kiss to Cas's mouth. "Never mind." He settles back down in Cas's arms and they both drift off to sleep.

**Notes for the Chapter:**

> Cas and Dean have moved on to the second season of Star Trek: TOS, and watched _The Deadly Years_.


	4. Chapter 4

When Cas wakes, he's disoriented. There's a warm body in front of him, and his face is buried in sweet smelling flesh. he opens his eyes and realizes he's holding Dean in his arms. He inhales deeply, letting the scents of leather, soap and gun oil wash over him. He's warm and comfortable, so he buries his face further into the back of Dean's neck and lets himself drift back to sleep.

Cas wakes again a little while later because Dean is moving. He tightens his arms, unwilling to let Dean go.

"Oof, Cas," Dean says in a sleep-cragged voice. "'M not goin' anywhere, just..." Cas opens his eyes and realizes that Dean has turned himself around, and they're facing each other. Dean's so close that he could count the freckles sprayed across his nose (57, he stores away for later), and he can see Dean's individual eyelashes. 

"Beautiful," Cas blurts, though it's not what he meant to say. Dean squirms a bit, lowering his eyes, but Cas won't let him get away with that. He tilts his head to follow Dean's eyes, and then when he's certain he's got Dean's attention, he captures Dean's mouth in a kiss.

"Hey Cas," Dean says after a minute. Cas huffs in laughter, unable to stop from smiling. They're still fully clothed, and Dean's white shirt is sleep rumpled. Cas wiggles his hands free and begins to slowly unbutton the shirt. Dean watches Cas's hands with great interest, his hands running up and down Cas's back.

Cas pushes Dean's shirt down to his elbows, but now that he's confronted with the broad expanse of Dean's chest, he's uncertain where to start. He has _ideas_ and _plans_ , but they're half-formed and he's not sure if any of them are right. 

He lets Dean explore his mouth and closes his eyes. He sends a panicked tendril towards where Jimmy's hiding out, knowing how weird this is, but not really caring because he just doesn't want to ruin it. 

 _Cas, what...?_ Jimmy asks, and Cas can practically feel Jimmy's eyes widen as he takes in the sensations that Cas is feeling. _Whoa. Cas. Are you sure you want me here...?_  

_Yes! Yes, tell me what to do._

_Cas, you know what you want to do, just... do it. You don't need me for this. Really._ Cas's attention is divided, mostly distracted by Dean's mouth and hands, which are roaming all over his back now, but he's also trying to pay attention to Jimmy.

_I do, Jimmy, I want to do this right._

Jimmy laughs. _Well, I guess since I got you this far..._ There's a long hesitation before Jimmy speaks again, and then when he speaks, his voice is a little bit rougher. _Think about... think about how you want to be touched. Then... then just touch him that way._

Cas is silent. 

 _Oh my. Oh, you don't know what you... Oh, jeeze. Well, okay, um._ Jimmy doesn't say anything for a long moment, and Cas feels that panic begin to rise, but finally Jimmy says, _Ok, start by just feeling his skin beneath your hands, okay? Just see what that feels like. And pay attention to what he does when you do that, because that will tell you whether he likes it or not._ Jimmy pauses again, and then mutters, _I can't believe I'm doing this..._

Cas does as he's told, running the palms of his hands across Dean's chest. Dean arches into the touch, eyes closed, and he murmurs Cas's name. Cas gets bolder, lowering one hand to Dean's abdomen and he can feel the muscles jumping and twitching beneath his palm. Cas watches Dean's face beneath hooded eyes and takes his cues from that: Dean bites his lower lip when Cas's hand drifts lower, exhales loudly when the hand drifts higher. Jimmy's giving him words of encouragement internally as well: _Yeah, that's it, Cas, just like that._  

“Cas,” Dean says, a low, drawn out sound, and Cas feels a surge of pride, because he’s making Dean sound like that, and he loves it. He loves the soft panting sounds coming out of Dean’s mouth, and he loves that Dean’s arching up into his hands reaching for more. He flattens his palms against Dean’s stomach and slides lower and lower until he’s cupping Dean’s erection through his pants. He sends a questioning thought towards Jimmy, who sends a strong affirmation back, and Cas squeezes lightly, puts a little pressure on Dean’s dick, and Dean groans loudly.

“Fuck Cas, that feels...” Dean says, breathing harder. “Just... keep doing that, okay?” Cas does, caressing and massaging Dean through his pants while he contemplates Dean’s chest, which is heaving in front of him. 

 _Cas, use your mouth,_ Jimmy says, and he’s a little breathless too, which Cas finds extremely interesting. 

 _Where?_ Cas asks. 

 _God, Cas, anywhere, just. Just fucking put your mouth on him, all right?_ Jimmy cries out in frustration. Just as he does, Dean grabs Cas’s head, pulling him upward so he can kiss him. The kiss is sloppy, all tongues and spit and Dean is writhing beneath Cas’s hands. Cas’s hips are rolling up and down on Dean’s thigh, and suddenly everyone is wearing far too many pieces of clothing. Cas slides his hand up again, and Dean whimpers a bit at the loss of sensation, but it turns into a happy groan when Cas slips his hand beneath the waistband of Dean’s pants, under his boxers to touch skin to skin. Dean is unbelievably warm and heavy, and Cas can feel the dampness of precome. He moves his hand up and down, forming a circle with his fingers.

“Cas, too... too many clothes,” Dean stutters. He tries to sit up, tries to force Cas to move, and even though Cas can be an unmovable force at times, he allows Dean to manhandle him into a seated position. Dean pulls his shirt all the way off and tosses it toward the laundry basket. Cas divests himself of his sweater, and they simultaneously reach for the buttons of each other’s pants, laughing when their hands get tangled together. Dean swats away Cas’s hands and undoes first his own, then Cas’s pants, and he kneels up to lower his pants and boxers. He does the same for Cas and shoves their clothing onto the floor.

They stare at each other for a long few moments, breathing heavily, pupils blown wide. The thickness in the air builds to a tipping point, and still they continue to stare. Cas can almost feel Jimmy roll his eyes and give him a mental shove. _TOUCH HIM, goddammit!_

Cas staggers forward and kisses Dean, grabbing onto his butt and pulling him close, gasping when their dicks come into contact with each other. _Oh_ , Cas thinks. _This. This feels really good._

Jimmy smirks. _Just wait, Cas. Try..._ Jimmy pauses, and then sends an image to Cas. Mentally nodding, Cas mouths at Dean’s jaw and down his neck to his clavicle. He tongues the indentation there for a long moment, massaging Dean’s ass at the same time. Dean’s grasping at Cas’s head, his fingers tangled in Cas’s hair, but Cas doesn’t seem to mind the pain. He spends a long time sucking Dean’s nipples into his mouth, first one, then the other, nibbling at them a little, then laving them with his tongue to soften some of the sting. It throws Dean a little bit off balance, and he tilts backward as slowly as he can until he’s prone, Cas lying on top of him. Cas kisses his way down Dean’s abdomen, sucking hard enough on the soft skin around Dean’s navel for small bruises to form. 

 _Talk to him, Cas,_ Jimmy says. _Tell him what you want to do to him._  

Cas pauses, wondering about the mechanics of talking while using his mouth on Dean’s skin, loathe to let one go while doing the other. _What do I say?_ There’s a humming sound as Jimmy thinks about it for a few minutes, and then several images - highly detailed - get pushed toward Cas. 

 _Any of those look interesting, Cas?_ Jimmy asks. Cas continues to lavish attention on Dean’s belly while he mentally examines each of the images. He shifts slightly in order to palm the globes of Dean’s butt, mimicking one of the images, nuzzling a little lower with his mouth. Dean sucks in a sharp breath. 

“Fuck, Cas, fuck, fuck, do that... do that again,” Dean says, and Cas smiles into Dean’s skin, where it’s warm and musky. He drags his tongue along Dean’s hipbone. 

“I have plans for you, Dean,” Cas says, his voice impossibly deep. Dean lets loose a long moan in response to Cas, and Cas takes the opportunity to shift one of Dean’s legs over his shoulder, just like the image Jimmy sent him. He can feel Jimmy egging him on, telling him he’s _doing it just right, just like that, Cas,_ and it’s beginning to sound a little like Jimmy is practically purring, he’s enjoying it so much.

Cas sucks one more bruise into Dean’s hip and stretches out on his belly. _Rock back and forth, Cas. It’ll feel... oh, it’ll feel so good._ Cas does, and Jimmy’s right, it does, the weight and friction on his own dick is _amazing_ , and he presses light kisses to the insides of Dean’s thighs. Dean relaxes into Cas, settles down a bit, but yelps when he feels Cas’s mouth on his balls. Cas sucks inward, imitating the last image that Jimmy sent him to the best of his ability. The image was the most clear, the most sharply detailed, with Jimmy writhing on the bed in their mind’s eye much in the way Dean was doing now.

Dean palms the back of Cas’s head as Cas sucks and nibbles away, and Cas can feel Dean’s thighs begin to shake. _Just like that, Cas, yes keep doing that,_ Jimmy’s encouraging Cas. Above him, Dean is babbling incoherently, the words falling from his mouth a torrent of profanity and Cas’s name. _Cas, try..._ and another series of images come flying his way, Jimmy’s head moving up the long legs of another man, Jimmy taking the man’s dick between his lips and swallowing down, and Cas obliges. Judging by the fever pitched noises coming from Dean’s mouth, it was the right advice, and barely seconds after Cas has sucked Dean down, his nose practically buried deep in the coarse hair at Dean’s root, Dean is coming down Cas’s throat, bellowing loudly. 

Cas rocks his hips back and forth once or twice, but before he can bring himself to orgasm, Dean’s pulling him up and kissing him, sloppy wide mouthed kisses. He grabs Cas’s dick and gives him one, two, three pulls with a twist at the top, his thumb grazing the slit there and Cas spills over, his orgasm surprising him in its intensity. Dean buries his face in Cas’s shoulder, and they both sit like that for a few long moments, breathing heavily.

"Cas, that was... Shit, that was amazing, man. Where'd you learn to do that?" 

"I didn’t, it was Jimmy’s idea."

Dean sits up, astonished. "What?! How the hell..." 

Cas kisses Dean. “That’s a good question. Hold on.” _Jimmy?_

Jimmy’s voice is sheepish. _Yeah, Cas?_

 _Um...I don’t know how to ask this, but..._ Cas sends the sensation of a question in Jimmy’s direction, and Jimmy responds with a sigh.

 _I was kind of adventurous in college._ Jimmy sounds embarrassed, ashamed about it, and Cas stiffens slightly.

“Cas?” Dean asks, stroking Cas’s back lightly. Cas just shakes his head.

_You don’t have to be embarrassed about it, Jimmy. It doesn’t change that you’re a good man._

Jimmy laughs. _I guess not, or else we wouldn’t be here together, would we?_

Cas sends the strongest wave of gratitude and affection toward Jimmy that he can. _Thank you, Jimmy. I mean that. Thank you so much. You have given me a great gift._ But Jimmy’s fading into the background again, leaving Cas alone with Dean. Cas decides to talk more with Jimmy later, when it’s just the two of them.

He explains to Dean what Jimmy told him, and Dean bursts into laughter, throwing his head back in his glee. “That’s... that’s priceless. That’s amazing, Cas.” He kisses Cas again. “Thank him for me, will ya?”

Cas nods, and he kisses Dean back, thrilled that he can do this, thinking of all the future kisses to come.

Dean laughs again to himself. “That Novak boy. Full of surprises.”

**Author's Note:**

> HUGE thanks to my beta, [clotpoleofthelord ](http://clotpoleofthelord.tumblr.com) and to [cliffnotesofanerd ](http://cliffnotesofanerd.tumblr.com) for the fantastic banner.


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